


Stupid Bet

by MistressPandora



Series: Tartan Terror Chronicles [3]
Category: Outlander & Related Fandoms, Supernatural
Genre: Anal Sex, BDSM, Belts, Bottom Dean Winchester, Crossover, Explicit Sexual Content, Friends With Benefits, Fuckbuddies, Impact Play, M/M, Mildly Dubious Consent, Panties, Plot What Plot/Porn Without Plot, Rough Sex, Safe Sane and Consensual, Spanking, Though the sanity is questionable, Top Jamie Fraser, Voice Kink, like really rough
Language: English
Status: Completed
Published: 2021-02-15
Updated: 2021-02-15
Packaged: 2021-03-13 17:14:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,050
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29405358
Author URL: https://archiveofourown.org/users/MistressPandora/pseuds/MistressPandora
Summary: Dean Winchester knew it was a stupid bet when he took it, but it did give him a less-awkward way to introduce something new into his friends with benefits arrangement with Jamie Fraser.
Relationships: Jamie Fraser/Dean Winchester
Series: Tartan Terror Chronicles [3]
Series URL: https://archiveofourown.org/series/1687324
Comments: 13
Kudos: 11
Collections: Outlander Bingo Challenge





	Stupid Bet

**Author's Note:**

  * For [LeviSqueaks](https://archiveofourown.org/users/LeviSqueaks/gifts).



> HAPPY BIRTHDAY LEVI!!!!!
> 
> This fic fills my Outlander Bingo Square **Panties.** Saved this one just for you, my favorite brother (from another mother).

It was a stupid bet. Idiotic. Dumb. If Sam were here, he'd have told Dean he was wrong from the get go. Dean wouldn't have listened, of course, and would have made the stupid bet anyway. And he still would have lost to Jamie Fraser. And then Sam would have laughed at him, like a lot, and said something supportive like, "I'm sure Jamie wouldn't _actually_ make you go through with it." He'd be right, of course, but that's not the point. And then he'd laugh at Dean some more.

The bet wasn't the issue. Dean hadn't exactly thrown it, but he knew he'd jumped to conclusions, knew he didn't have all the facts. He still defended his premature position, even after he knew it was probably wrong. _Werewolf_ just made so much more sense than _cú síth_ , if for no other reason than this was Montana, not freaking Scotland. Nevermind that Jamie was intimately familiar with cú síth and knew exactly what their M.O. was. Dean knew all that, but his stubborn pride kept him from conceding the point.

Dean also knew he really wanted to lose this bet. The terms were too perfect. He'd spent a month trying to figure out how to introduce this into the casual whatever-the-hell it was that he and Jamie had going on. But how was one man supposed to tell another man that he sometimes liked to wear lacy panties? That he got off on the very distinct feeling of confinement, on the contrast between the rough inside of his jeans and the delicate lace stretched tight across his skin. 

Nevermind that Dean and Jamie had been fuckbuddies off and on for about two years now. It was one thing to offer to give your friend a blow job or to trade shower handies after a particularly nasty hunt. Even dropping something like, “Hey, man, you know you could beat my ass if you wanted,” was fine. Pissing each other off and working it out with a good old-fashioned rage bang and wrecking a motel room? Sure. But what was he supposed to say about _this?_ “Sometimes I like to wear pretty underthings and the whole time I’m thinking about you seeing it and it makes me so hard it hurts?” Fuck no.

This bet was just too convenient. And the best part was that Jamie had suggested it, unprompted, having no idea that Dean was already into it. Jamie had even _produced a pair of panties_ from his duffle bag for the purpose. In Dean’s size. Not that Dean was a small man, but Jamie was just plain gigantic, so they couldn’t have been his for his own use. 

Dean had made a show of doubting that the panties—black lace with a high leg and a low waist—would fit, but Jamie hadn’t been remotely convinced. So they’d found conclusive evidence that Jamie had been right and it was a cú síth, not a werewolf. And then they’d ganked the thing, fighting together in that comfortable way that Dean had come to understand was a rare form of trust. 

Not to mention it was damned fun to watch Jamie wreak absolute havoc on monsters while wearing a kilt and swinging a broadsword. By the time they'd gotten back to the motel, the adrenaline was wearing off and they were both dead tired but still too riled up to collapse. Besides, Dean had spent the drive back thinking about those panties. He and Jamie didn't speak much, which wasn't unusual or awkward. Jamie wasn't very chatty after a hunt normally, and Dean knew he had a rather nasty history with this sort of monster.

So Dean took the first shower when they got back to the motel, washed the blood and grime and ichor from some truly obscure places. When he came out of the bathroom with a towel around his waist, Jamie gave him a long look up and down, eyes dark with lust. Then he shut himself in the steamy bathroom and turned on the water.

Jamie had laid the black panties on top of Dean's clean clothes. He tossed the towel onto the floor and ran his fingers over the lace. After a hunt, after being rough and gross and beat to hell, the delicate fabric felt soft against his skin. It was a nice contrast. Dean slid them on and had to bite the inside of his cheek to keep from making any obscene noises. The panties fit him well, curving over his ass and holding his dick rather securely against his body. He pulled on a clean pair of blue jeans and a plain long-sleeved shirt, and tugged on his boots. 

Knocking twice on the bathroom door, Dean called, “Running across the street for beer and grub, back in a minute.”

“Aye, then,” Jamie answered over the sound of the shower. 

When Dean returned with a six pack of beer and a sack of truckstop staples, Jamie wore just a thin pair of pajama pants, his feet and scarred torso bare. Dean had seen Jamie half naked—and completely naked—many times, had even brought the sight of him to mind on more than one quiet evening alone. But every time, Dean had the same thought: _Freaking hell, how did someone get so ripped on the road?_ Jamie’s Greek god abs twitched as he toweled off his unruly mop of ruddy hair and Dean tried not to stare too much as he offered him a bottle of beer.

They shared a bag of beef jerky, shooting the shit and killing two beers each, then passing Jamie's flask of scotch back and forth. It was easy and comfortable between them, like it always was. They weren’t dating by any stretch of the imagination. Neither of them were in any kind of position to be in a relationship with anyone, not even each other. But there was a definite mutual attraction there and the sex was fantastic.

“Ye’re wearing them, aren’t ye?” Jamie’s eyes were smiling at Dean though his mouth was busy drinking his third beer, lips wrapped around the bottle. The panties made Dean mentally replace the bottle with his own cock.

Through an impressive display of willpower, Dean did not adjust himself even though he was getting what promised to be a rather impressive boner. “A bet’s a bet,” he said coolly.

“Can I see?”

Fighting against the urge to rip his own clothes off in a rush, Dean tipped his beer back and drained it, depositing the empty bottle on the table with the bag of trash and the growing pile of empties. Standing, he pulled his shirt over his head and off, moving slowly, drawing it out for Jamie’s benefit. Well, for his own too. Dean liked to feel Jamie’s eyes on his body. The sensation of exposure combined with being the object of the man’s desire gave him a thrill. 

Dean hadn’t put on a belt, and his jeans rode low on his hips. He unfastened the fly and turned his back to Jamie, letting his pants fall to a puddle around his ankles. Bending over to really let the panties do their job making his ass look good, Dean worked his feet free and kicked his jeans out of the way. He straightened and turned back around to face Jamie again, wearing nothing now but the panties, stretched taut and straining over his hard cock. Saying nothing, he spread his hands by his sides in a gesture meant to ask, _Well, what do you think?_

Jamie swallowed hard and he _did_ adjust himself, his pajama pants doing absolutely nothing to obscure the outline of his erection. “That’s no’ exactly what I expected ye to do, but I willnae complain about it, that’s for certain.” He looked Dean up and down and back up again, a grin spreading across his handsome face. “Aye, that’s one for the spank bank.” 

Just to play it up, Dean put his hands on his hips and affected an air of offense. “Don’t objectify me.” It was as much to break the tension as to deflect both of their attention away from the fact that Jamie’s reaction had made Dean flush with pride and his heart skip a beat. 

“Aye, _a charaid_ , I’m sorry. I didnae mean it like that.” Jamie rose and came to him, skimming his hands over his sides, around his waist, and then over his ass. He dug his fingers into Dean’s flesh through the lace, making the panties pull tighter against his hard cock. “If I fuck ye good, will ye forgive me?”

“You… like it?” Goddamn it, why did that come out so shy? _Get it together, Winchester. This is Jamie, not someone you need to impress._

“See for yerself.”

Dean slipped his hand under the waistband of Jamie’s pants and palmed his naked cock underneath. Jamie’s dick was thick and hard, and he moaned when Dean closed his fist around it. Dean wanted him. God, did he ever want him. He closed the narrow distance between them and pressed an open-mouthed kiss to the crook of Jamie’s neck, sinking his teeth into his skin.

Jamie hissed and tightened his grip on Dean. His skin bore the faint aroma of some off-brand shower gel and shaving cream, and the bitter, war-like taste of blade oil and gunshot residue that never really came off. Need, desire, a wild animal lust shot through Dean, burnt his insides like a flamethrower and left nothing behind but smoldering desperation. Dean sucked and bit a hard mark into Jamie's throat, and Jamie groaned, his rough hands wandering Dean's body with fierce possessiveness. 

The hunt hadn't been as clean as either of them would have liked, and while the booze was helping dull the sharpest of the sting, Dean needed more. He needed to be worked over, needed to purge all the nightmare fuel from his mind. Jamie was good at that. Dean liked to relinquish control, found release in it. Jamie liked to seize it, liked to leave Dean a trembling, sobbing, begging mess. Survival is what it was, and it worked for them. 

"Fuck, Jamie," Dean groaned when Jamie slid his middle finger down the crack of his ass, teasing him. "Please make it hurt. I don't want to be able to sit tomorrow." He switched sides and sucked another bruise into Jamie’s neck.

Jamie grabbed a fistfull of Dean’s hair and pulled him away from his neck, holding him at a rather uncomfortable angle. “Did I give ye permission to mark me?”

Hell yes, it was going to be one of those nights. One of the truly rough nights where they took out their stress on each other, egging the other on and fucking hard till they both just gave out and then slept for a whole day. Sometimes feeling alive and human and connected was enough. But one of the victims that they hadn't saved had been a woman with dark hair, and that always seemed to mess Jamie up real bad. Dean would rather leap into the cage with Lucifer than ask why, but he figured it had something to do with Jamie's long-dead wife.

"And what are you gonna do about it, huh, Big Red?" 

Jamie pulled Dean’s head farther to the side, threatening his balance. It almost hurt, but mostly it just made his heart beat faster and his cock twitch against its lace prison. “Tough talk from a man in yer position. On yer knees, Winchester.” He clamped one strong hand on Dean’s shoulder and shoved him toward the floor.

Dean lowered himself to his knees, losing control of his descent at the last second and wincing when his knees hit the threadbare carpet. He wasn’t really a big fan of giving blowjobs, but for Jamie he often made an exception. He tugged down on his pajama bottoms, and once face to face with Jamie’s hard cock, Dean’s mouth began to water. All he wanted was that dick inside of him somewhere, and he didn’t really care where. He took the head into his mouth without any preamble whatsoever, just dove right in, moaning like he was starved for it.

The fist in his hair loosened, but held him firmly in place so he couldn’t back off. Jamie thrust into his mouth, groaning. “This is what I’m going to do about it. I’m going to use ye as I see fit until ye beg me to let ye come. Starting with this smart mouth of yers— _Christ_ , yer mouth.”

Okay, so maybe under certain circumstances, Dean _did_ enjoy sucking cock. Judging by Jamie’s reaction, he was pretty damn good at it too. A drop or two of precome hit his tongue, and Dean stuck one hand down his panties to stroke himself. 

Jamie swatted him lightly on the cheek. “Dinna touch that, it’s mine.”

Dean whimpered, gave himself one more quick squeeze, and withdrew his hand, letting out an annoyed grunt. He could feel Jamie getting close already. 

"That's enough," Jamie said, voice rough with desperate arousal. Dean didn't stop though. He wrapped his hands around Jamie's hips and held on, gagging when it forced the head of his cock into Dean's throat. If this thing between them were gentler, he might have done as he was told. But they had safe words for a reason, and they'd given each other the green light months ago to push limits. Jamie would say, “MacKenzie,” if Dean went too far.

“Aye, I said stop, ye insolent brat.” Jamie clamped his hands on Dean’s wrists and pried him off, shoving him toward one of the beds, getting rug burn on his bare thighs. “I ought to beat that pretty arse red.”

"Do it, then, tough guy," Dean said, sprawled against the deceptively sturdy bed frame. The fall actually hurt a little, but it just stoked his wild desire hotter, excited him more. Just to be a shit, Dean straightened a leg and tripped up Jamie in his own pajama pants. The floor shook when the big guy fell.

"Oh, ye'll pay for that." Jamie scrambled free of his clothes and wrestled Dean to the floor, laying on top of him with all his weight. Dean squirmed and struggled, just on instinct, but Jamie pinned his arms down, pressing the length of his naked body on top of him. Hovering inches from his face, Jamie grinned down at him, feral and horny. "Keep wriggling like that, it’s exciting."

“Fuck you, Braveheart.” Dean thrust up with his hips and grinded his dick against Jamie, earning him a jab in the thigh with his cock. It had the desired effect, and Jamie tightened his grip, dipping his head to sink his teeth into the bend of Dean’s neck. He bit him hard, and Dean hissed in pain. He didn’t feel the skin break, but shit.

“Nay,” Jamie said, his teeth scraping over Dean’s flesh. “But I’ll fuck ye and ye’ll thank me for it, will ye no’?”

“Not if you don’t get on with it.” With a grunt of effort, Dean managed to get enough leverage to roll Jamie onto his back, following through and landing on top. He let out a triumphant, “Ha!” and worked a hand between their bodies, getting a firm—if careful—grip on Jamie’s balls.

Jamie groaned, but swallowed it down. “Dinna get smug, I let ye do it.”

Dean sneered down at him. “Yeah, sure you did.” He teased against Jamie’s ass with one finger. “You sure you don’t want me to fuck you this time?”

With a growl, Jamie got a knee up against Dean’s chest, an iron grip on his wrist until Dean let go of his balls. Then that gigantic man shoved Dean off of him, landing in a crouch over him, and calmly walked to his duffle bag tossed on the other bed. The hardware of his belt jingled.

It took Dean a few precious seconds to recover. If Jamie had tossed him any harder, Dean would have been gasping like a landed fish. 

“On yer feet,” Jamie ordered in the voice he used when the police didn’t want to do what he said. Dean rolled over and groaned, climbing to his feet with an arm braced against the bed. Jamie had his belt in one hand, doubled up, and a legitimate bolt of fear flashed through Dean, but only for a split second. Then it was just excitement and anticipation and need.

Jamie shoved hard at Dean’s back and bent him over the bed. The belt crashed into his ass less than a second later, a resounding _crack_ that Dean heard before his brain could register the pain. But oh God, the pain. 

“Mother _fucker!”_ Tears sprang to his eyes before he could decide if the pain was good or bad. He fought it on pure instinct, tried to scramble away, but Jamie swept his feet out from under him with his leg and held him pressed to the mattress with an arm.

“Hold still, ye wee shite. Ye’re making it worse than it has to be.” 

The belt came down again, hard and stinging and Dean cried out. “Make it worse then, you son of a bitch.”

Another blow. Holy fuck, he was going to be bleeding in the shape of the lace pattern. Tears fell down Dean’s cheeks, hot and involuntary.

“That was verra rude.” Jamie whipped him again. The belt sent hot flames of pain through Dean's backside.

Dean cried out, a wordless noise like an animal, any taunts or insults he might have thrown back at Jamie trapped in his throat by the delicious pain. Holy shit, it hurt so good. Dean rutted awkwardly against the side of the bed because that's all he could do with Jamie's powerful arm holding him down and his toes slipping on the carpet. The cheap motel blanket was rough on his dick through the panties, but Dean didn't care. It was silky smooth and perfect compared to the absolute havoc Jamie was wreaking on his ass with the belt.

The belt crashed into him again, blinding pain, tears pouring down his cheeks. Then the sound of the crack, and Dean’s hoarse cry. “Stop yer thrashing,” Jamie ordered “I’ll give it to ye when I’m good and ready.”

Anything. Dean would have done _anything_ to come just then. He almost did. The mattress and the panties and the pain and Jamie Fraser’s fucking _voice_ were nearly sufficient. “Please,” Dean said. Or rather, he tried to, but he couldn’t catch his breath enough to say it. His mouth moved, but no sound came out.

Jamie leaned over him, his strong arm still pinning him to the bed. “What was that?”

“Please,” Dean managed to croak out. “I can’t—” he tried to push himself up but he was trembling and couldn’t get purchase. If Jamie was pulling his punches, no fucking wonder he had such a high kill streak. Goddamn. “Fuck me,” Dean begged. The real exhaustion was setting in, his body all out of adrenaline.

“Aye,” Jamie said, panting and clearly worn out too. The cú síth had put up a hell of a fight. “I’ve got ye, Dean. Dinna fash.” 

The belt landed on the floor near Dean’s feet and then Jamie’s arm looped around his waist, dragging him to his feet and then shoving him face-first onto the bed. At least he was _on_ the bed this time, the crappy old mattress springs shrieking. Dean wriggled, tried to work his panties off, but his hands were still shaking and his grip was too clumsy. Not to mention the flesh of his ass felt like it was melting. He growled and whined in frustration, but Jamie rescued him, dragging the lingerie off easily.

More squeaking springs as Jamie knelt on the bed over him. He slid a lubed up hand down Dean’s ass crack, and dipped one finger briefly inside him. Dean groaned and pushed back, desperate for more. “I’m fine, just do it,” Dean said, his face pressed into the mattress. 

Jamie settled on top of him, sinking his slick cock into Dean, filling him. His movements were slow but firm. And when he was all the way in and their bodies flush together, Jamie wrapped his arms around Dean, holding him tight. His solid weight, the feeling of so much skin contact, even the sound of Jamie’s breathing went a long way to soothe Dean’s flayed nerves.

“Christ, ye’re hot,” Jamie growled into Dean’s ear. Whether he meant physically warm or attractive, Dean wasn’t sure. Jamie licked along the shell of his ear and Dean shuddered. 

Everything disintegrated into a haze of decadent sensation. Painful welts from the belt under Jamie’s hips compounded the burn and stretch of his cock sliding in and out of him in sure strokes. Jamie’s hot breath tickled the back of Dean’s neck. The rough, possessive grip of Jamie’s hands on his chest. The unmistakably rhythmic protesting of old bed springs. The rough blanket under his cheek that Dean tried not to think too hard about. Jamie’s hand trailing down his torso to wrap around Dean’s cock even while he fucked him firmly into the mattress.

Dean let out moan after wordless moan, occasionally managing a, “fuck,” or a, “Jamie, shit,” in between gasps. His tears hadn’t really stopped, just everything, all the stress and the fear and the regret and the physical pain had no other outlet. Dean didn’t bother to fight it. 

He didn’t bother to fight his orgasm either, the ecstasy burning through him, shouting Jamie’s name until Jamie bit down hard on Dean’s shoulder. Jamie came right after, growling something in a muddle of languages in Dean’s ear.

For a time, Jamie just laid there shuddering and panting on top of Dean, his dick still inside of him. It might have been Dean’s imagination, but he thought he could feel Jamie’s heart tapping away against his back.

At last, Jamie pulled out, rolling onto the bed next to Dean but still very close. He tied off a condom that Dean didn’t recall him putting on in the first place, and tossed it toward the trash can. He might have made it. Dean wouldn’t put it past him.

Dean covered his face and groaned rather pathetically into the crook of his arm. He’d stopped crying—finally—but still sniffled and breathed heavily. 

Jamie pulled Dean into his arms again, making shushing noises like he was calming a wild animal or comforting a child. Dean let him wrap him up, let him hold him and stroke his hair and rub circles over his back and arms. He buried his face in Jamie’s sweaty chest and breathed him in. It was just touch and comfort and sex between them, nothing else. And that was okay, it worked for them. 

They rarely kissed, almost never on the mouth. Jamie pressed a lingering, rather sweet kiss to the top of Dean’s head. “I’ve got ye, _a charaid_. Rest easy now.”

Dean was nearly asleep anyway, worn completely out and sated, the heat of Jamie’s body enough to send him merrily toward unconsciousness. “No chick flick moments,” Dean muttered.

Jamie lightly swatted the back of Dean’s head. “Shut up.”

“Okay, but I’ve gotta ask,” Dean said. Every inch of him was worn out and raw, but he’d never sleep until he got the nagging question out of his mind.

“Hmm?” 

Maybe Dean didn’t really want the answer to this, but he also really wanted the answer to this. “How did you know?” 

“How did I ken what? Yer size?” Jamie asked, voice rumbling and drowsy.

“Well… for a start. Yeah.”

“Four months ago, that wraith job in Oklahoma?” Jamie said.

“Yeah…” Where the hell was this going?

Jamie yawned, not bothering to cover it. “Ye had me get the first aid kit out of yer bag and I saw a pair in there. Later when Sam was sleeping off the codeine and you were in the shower, I looked again.” His big shoulder twitched in a shrug.

“So… you’ve been planning this?”

“More or less.”

“Huh.” Dean yawned too. “Kinky son of a bitch.”

Jamie snorted. “Ye’re welcome.”


End file.
